Cherry Cheeks

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Spanked Outside Switched Caned Outdoors - Cherry Cheeks

Miss Sephie and Missy go on a walk with a friend, and would it really be a walk without some switching? Don’t miss this full video of Missy’s long, thorough switching outside by the scenic river! Discipline is anywhere, any time, after all! Watch Missy wiggle a whine as the switches whack away at her vulnerable bottom!

Miss Sephie, Missy

Resolution : 1920×1080
Duration : 00:09:20

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Sissy Maid and French Maid Spanked by Miss Sephie - Cherry Cheeks

Maid Missy and sissy maid Jesse have been slacking on their chores around the house! Miss Sephie makes them hold up their skirts whole she spanks their naughty bottoms side by side! First she uses a bamboo rice paddle, followed by a wicked plastic wooden spoon! Finally she uses the heavy silicone spatula, but she isn't done yet! To really settle in the lesson, she uses the birch on their naughty sore bottoms and the soles of their feet!

Jesse, Miss Sephie, Missy

Resolution : 1920x1080
Duration : 00:06:23

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Sorority Sister Pledge Paddled and Plugged - Cherry Cheeks

Head of the Sorority sisters has chosen a pledge to bully! She chooses to make a video for the pledge, scolding the camera as the girl lays over her lap so that she won't ever forget this spanking! The sorority has standards, and the pledge has been lazy! She paddles her without mercy with a wood pickleball paddle, but that's not enough! She then a butt plug into the pledge's tight ass, mocking and humiliating her as she paddles her more, with a frat paddle, every swat a reminder that the plug is in! Bonus paddling over the sink!

Miss Sephie, Missy

Resolution : 1920×1080
Duration : 00:06:15

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THE Hardest F/F Spanking and Anal Punishment - Cherry Cheeks

VERY SEVERE. NOT FOR THE FAINT OF HEART! You have been warned. When Missy first met Miss Sephie, she had a LOT of personal issues to overcome. They face these issues with HARD discipline. Miss Sephie starts out with the hairbrush, no warm-up for that naughty bottom, before moving on to the bath brush, followed by the wooden spoon, jokari paddle, and many more. Missy then bends over the back of the van for Miss Sephie’s HARD paddling. Bending over the hood of the van, Miss Sephie uses the cane on Missy’s thighs. Next is a between the cheeks punishment. She starts with a hard anal hand spanking, then she instructs Missy to reach back and spread her own cheeks. Next is the riding crop, and then the handle of a wooden spoon to cane Missy’s poor little bum hole. Although it all hurts terribly, Missy pushes through the pain as her heart’s hurt out-weights the physical pain she is enduring. Miss Sephie finally sits on top of Missy’s back to stretch out her bottom hole and spank her some more. In the next punishment, Missy learns about apologizing correctly, and not being passive aggressive. This is a HARD anal punishment, starting with Miss Sephie’s hand and moving on to the nubbed metal probe. Missy’s next punishment is on an already marked bottom. She takes the bath brush for a spanking, and then is anally punished with the handle of it! Miss Sephie promises no mercy, as she uses the metal probe next. Last of all, Missy takes the metal bat anally!

Miss Sephie, Missy

Resolution : 1280×720
Duration : 00:57:51

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3 Girls Spank Their Bratty Roommate - Cherry Cheeks

Miss Sephie, Madame Ami, and Parker want to go out to have fun, but first they must confront their naughty brat of a roommate, MISSY! The girls are all done up to go, but they bend Missy over a pillow and flip up her short skirt, pulling down her skimpy panties. Each roomie chooses 2 implements to warm Missy’s bottom with, and make Missy roll a dice for each one as they take turns turning her ass a cherry, sorry red! Rubber tawse, rug beater, leather strap, wood spoon, silicone paddle, and more!

Ami, Miss Sephie, Missy, Parker

Resolution : 1920x1080
Duration : 00:09:14

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Dixie Spanked by Mom OUTSIDE - Cherry Cheeks

Troublemaker Dixie gets a bare bottomed spanking outside for being a brat!

Dixie, Miss Sephie

Resolution : 1920×1080
Duration : 00:03:41

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FF Anal Part 1 - Cherry Cheeks

Nothing but the naughtiest bottom-holes are plugged, probed and pegged in this video! Miss Sephie teaches Missy what REAL anal discipline is supposed to be along with some role play discipline scenes, just because they can, or simply tests of endurance!!! How much stretching can Missy really take? What is the largest probe of them all? Watch and find out! Also includes rare footage with our blonde Amazonian friend Kira whom probes Missy's anus and get equally embarrassed as Missy returns the favour!

Kira, Miss Sephie, Missy

Resolution : 720x480
Duration : 00:52:19

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FF Anal Part 2 - Cherry Cheeks

Nothing but the naughtiest bottom-holes are plugged, probed and pegged in this video! Miss Sephie teaches Missy what REAL anal discipline is supposed to be along with some role play discipline scenes, just because they can, or simply tests of endurance!!! How much stretching can Missy really take? What is the largest probe of them all? Watch and find out!

Miss Sephie, Missy

Resolution : 720×480
Duration : 00:57:05

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Maid Missy gets Spanked and Pegged - Cherry Cheeks

Miss Sephie came home ready to go to a party, but Missy got dressed up for the party instead of cleaning! Miss Sephie won’t take this lightly, and she immediately gives Missy a HARD spanking with a wooden spoon! Picking up Missy’s skunk-feather duster, she probes her naughty bottom-hole while scolding her. Unsatisfied, she grabs a wooden hairbrush and paddles Missy’s sore bottom with it over the stool! Then, Miss Sephie orders Missy to do the dishes while having her ass probed by the Stinger on a stick WHILE doing the dishes! Finally, Miss Sephie uses her BIG black dong to give Missy a THOROUGH discipline pegging—while Missy is still doing dishes!

Miss Sephie, Missy

Resolution : 1280x720
Duration : 00:18:52

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Real Discipline for Missy: Hairbrushings - Cherry Cheeks

Four REAL Discipline sessions for Missy, given by Miss Sephie, all with various wicked hairbrushes. Missy is scolded for not doing her homework, missing a test, needing motivation, and texting while driving, receiving a hard bare bottom spanking with different hairbrushes after each time!

Miss Sephie, Missy

Resolution : 1920x1080
Duration : 00:14:56

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